An Efficient Synthesis of Achiral and Chiral 1,2,4-Triazolium Salts: Bench Stable Precursors for N-Heterocyclic Carbenes

Abstract

The promising utility of triazolyl N-heterocyclic carbene catalysts in umpolung aldehyde chemistry requires a straightforward reliable synthesis from readily available materials. Herein, we describe the synthesis of a variety of triazolyl N-heterocyclic carbene precursors. The reactions commence from commercially available amino acids and proceed in 44−68% overall yields. The N-heterocyclic salts are air-stable crystalline solids that can be stored with no special precaution and can generate the active catalyst when treated with an appropriate base.